Career

How to Convince Your Boss to Let You Work Remotely (Worksheet Included!)

It’s no secret: Remote work is becoming a lot more common. In fact, 70% of professionals around the world are working remotely at least one day each week, according to a recent study. And some are even working remotely full time.

One of the biggest benefits of remote work is the flexibility it allows you in other areas of your life. Sick of where you live now? Move somewhere totally different. Need to take care of a parent who lives in a different state? You can do that. Want to be one of those people who hops from beautiful beach to medieval city to cozy cabin? That’s an option, too. Working from anywhere in the world has become so popular that you can even participate in a work travel program that plans your itinerary and sets you up with co-working space.

Of course, there are some occupations where you’re unlikely to be able to work remotely—healthcare providers, emergency personnel, and so forth. And there are some companies where remote work is frowned upon, if it’s even an option at all. But there are plenty of other roles and places where you can, as long as you have a laptop and reliable internet.

The tricky part is finding one of these lucky gigs. But you might not have to leave your current job to make your remote work dreams come true. We’ve put together some tips on how to ask your boss if you can work remotely—from anywhere at all on the planet—full time. Because yes, you can do this.

Step 1: Make Sure You’re a Top Performer

Typically, it’s better for your employer to hang on to you—someone who knows the company and the job—than to hire and train someone completely new. But that’s only if you’re already a top performer. If you’re not, it doesn’t make sense to have this conversation at all. If your boss doesn’t trust you now, when you work in the office and under their watch, it’s highly unlikely they’ll trust you when you’re gallivanting all over the globe.

So before you make this ask, consider the following:

  • How have your past few performance reviews gone?
  • Have you ever dropped the ball? If so, how did you recover?
  • What other positive feedback have you received?
  • How’s your rapport with your co-workers and/or clients?

If you think the answers to these questions prove that you’re the absolute best employee you can be, write down some talking points so you can whip them out when you make the ask.

If these answers don’t show you in a good light, don’t lose all hope. Instead, use this as an opportunity to figure out why you’re not performing up to par and start focusing on improving. And maybe, just maybe, you’ll be better set up to have this conversation someday in the near future.

Step 2: Get Clear on Your “Why”

Kyle, a marketing executive at a Fortune 100 financial services company, wanted to telecommute full time so he could relocate to his hometown. It was never an option he’d considered before—he felt that working remotely had the stigma of “you’re lazy or a slacker.” But that changed after a trip home to visit family. “My mother had reached retirement age and my two siblings had moved away,” Kyle shares. “So I wanted to be closer to home.”

I’m a big believer that you don’t have to justify every choice you make, feeling you feel, or question you ask. But let’s face it: If you walk into your boss’ office and make this request, they’re going to ask for a reason. Not just because they’re curious, but because this potential change affects them and your teammates, too.

Your reason can be a variety of things. And no—it doesn’t have to be as altruistic as Kyle’s, nor do you have to get into the nitty-gritty of it all. But be clear on what it is. Even if it’s that you want to explore the world or live in a different city than where your office is.

Don’t be ashamed to prioritize the non-work parts of your life. An employee who’s better able to manage other stresses [and aspects of their life] will be higher functioning and more focused.

Kyle

“Don’t be ashamed to prioritize the non-work parts of your life,” Kyle says. “An employee who’s better able to manage other stresses [and aspects of their life] will be higher functioning and more focused. Don’t be afraid to ask for arrangements that work better for you.”

Getting clear on your motivation will also help you put things into perspective if your boss eventually says no. Is this a deal breaker for you? What would your next step be? Have you already scheduled a move-out date and booked flights to Honolulu? Even though I’d love for your boss to give you a resounding yes, the truth is that not all dreams come true. Know what your backup plan is ahead of time so you don’t get caught off guard and start panicking.

Step 3: Put Together a Plan

Being able to anticipate any questions or concerns your boss might have—and providing potential solutions—can go a long way. It’ll show that you’ve put a lot of thought into this and considered not just what you want, but how this could impact others and your work.

“Put yourself in your manager’s shoes,” says Lizz Vo, a communication specialist who successfully requested to work from a different location. “What concerns would she have and how can you address them?”

Put yourself in your manager’s shoes. What concerns would she have and how can you address them?

Lizz Vo

So what are some potential concerns? Emily Ascani, a manager who has approved a few of her employees’ requests to work remotely full time, mentions communication.

“If someone isn’t in the office, being available for communication via video conferencing and Slack is crucial to the team’s success,” Ascani explains. “We rely heavily on video conferencing with our offshore teams and remote employees.”

Another common worry is productivity. With all those devilish temptations—napping on the beach, skiing on freshly fallen snow, exploring a brand new city—how will you get anything done?

Asking yourself questions like these—and preparing answers for them—should help you go in well-equipped for your boss’ potential rebuttals:

  • How will you define your work hours? When will you be online or otherwise available to your manager or team (and how will you account for time differences)?
  • Where will you be working, and how will you ensure you’re staying focused and on task?
  • How will you attend or be involved in relevant meetings and important conversations or gatherings?
  • What is your plan for maintaining regular communication and interaction with your boss and other co-workers?
  • Think about the biggest work conflicts or issues you’ve faced: How would you handle them differently as a remote employee?
  • How will you compensate for being apart from your company’s office culture and continue to uphold strong relationships with your colleagues, manager, and clients?

To make your life even easier, we created a free downloadable worksheet to help you plan out everything you need to make the ask.

Step 4: Have the Conversation

The time has come. The meeting’s on the calendar, you’ve concluded that you’re a pretty darn good employee, and you’ve prepared as comprehensive a plan as possible. The only thing left to do is, well, ask.

First off, “avoid making the [entire] conversation about you and your needs,” says Kiera Abbamonte, a content writer who asked to relocate when her partner was offered a promotion in a different city. Because realistically, your boss cares less about what you want and more about how you’ll meet what they want.

Here’s where that first step—evaluating whether or not you’re a top performer—comes in.

“Highlight the unique stuff you bring to the role, such as past successes,” Abbamonte says. “Sell your employer on helping you find a better working situation,” and why that’s a better solution than finding someone to replace you.

Highlight the unique stuff you bring to the role, such as past successes. Sell your employer on helping you find a better working situation.

Kiera Abbamonte

And, of course, don’t forget to present your plan. Ultimately, what’s most important is proving that, no matter where you’ll be working from, you’ll be just as productive (if not more productive).

Lastly, leave some room for them to ask questions and express any further hesitations. You’re not a mindreader, so chances are you haven’t thought of everything (and that’s OK). You’re making a pretty big ask here, so if they want to clarify anything or set up follow-up meetings, let them.

Step 5: Suggest a Trial Run

If your boss is open to the idea of you working remotely full time but not completely comfortable with it, offer to collaborate with them to come up with a solution that works for everyone. One option: Suggest a trial period. Shivan Barwari, who asked if he could work remotely so he could travel around the United States, did just that.

During your trial run, “be sure you can still produce the same amount and quality of work or your leash will be pulled back quickly,” explains Barwari. For Barwari, who does a lot of video and image editing, making sure he could be just as productive meant finding a strong internet connection, buying a good desk and wireless mouse, and figuring out how to log in remotely to his company’s system.

Be sure you can still produce the same amount and quality of work or your leash will be pulled back quickly.

Shivan Barwari

Perhaps you start with working away from the office once a week or see how it goes for a full week or two before your manager makes their final decision. This trial period is a chance for you and your boss to figure out what works and what doesn’t work when you’re not in the office, and it’s an opportunity for you to work out any kinks (like figuring out what to do when your Airbnb’s WiFi goes down). And hey—you might find that you don’t even like working remotely. Better to figure that out during a test run than when it’s permanent, right?

Going from being in the office every day (or most of the time) to barely ever seeing your co-workers in person is a big change. And while I’m a big supporter of this lifestyle, your boss may not necessarily be on board 100%. But if you’re thorough and respectful, you might just get the answer you’re looking for.

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